The evolution of YOLO

The price of anything is the amount of life you exchange for it.

Welcome entrepreneurs. I’m so glad you’re here. 

One of the most powerful practices in the human journey is to contemplate your own death. It might sound morbid, but it’s been a core practice in nearly all the world’s wisdom traditions from stoicism to Buddhism, from Christianity to existentialism. 

For a long time, when I considered my own mortality I felt a profound need to push harder. To fit more in. I think that’s what most people expect from the exercise.

But these days, that’s changing. That’s what I want to explore today – how our relationship to our own death changes, the closer we get to it.

---

The Evolution of YOLO

How do you feel when you hear the term “YOLO”?

”You only live once” became a thing when I was in my 20s, and when I first heard it, I felt seen. 

YOLO lit a fire underneath my ass. You only live once. Damn right. So you’d better get fucking moving. Better work more, play harder, travel more, see all the things, say all the things. Live the most full throated existence you can. YOLO activated the part of my brain that was convinced I needed to pack in maximum experience and impact before my lights were turned out for good. 

There’s this quote I love, from Augustus, which starts like this: 

The young man, who does not know the future, sees life as a kind of epic adventure, an Odyssey through strange seas and unknown islands, where he will test and prove his powers, and thereby discover his immortality. 

And then, about six years ago, I found myself crying in bed after watching an Adam Sandler comedy special. He mentioned that he’d turned 50, and I never felt so old. When I looked back at my own life in that moment, I saw accomplishment, sure, but more than that I saw the infinite number of things I hadn’t done yet. And I felt panicky. After watching the middle-aged star of Happy Gilmore spout raunchy humor for an hour, I lay in bed grappling with something closer to the second part of the Augustus quote: 

The man of middle years, who has lived the future that he once dreamed, sees life as a tragedy; for he has learned that his power, however great, will not prevail against those forces of accident and nature to which he gives the names of gods, and has learned that he is mortal. 

By then I knew that YOLO cuts both ways. It’s both a rallying cry and also, at some point, an admonition. If you only live once, you will never again get a chance to make the impact you could have made. In spite of all I had accomplished, my mistakes in career and relationship loomed large, and I couldn’t help but see my own failure to measure up in Sandler’s reflections, made palatable through potty humor, about his own career and life. 

Am I a comedian? Does it even make sense that I would measure myself against Adam Sandler?

Of course not.

But my achieving mind gets its juice through comparison, and anyone and everyone is fair game (as long as they’ve achieved more than I have. To those who haven’t, I’m somehow blind).

YOLO hits different at different stages of life. 

Death is the penalty we pay for the privilege of life

The other week I unexpectedly found myself with a free-day, which I spent in a cabin by a pond in the woods called, appropriately, “Thoreau.” I’ve had occasion to consider my own mortality recently, as a handful of my friends and family are simultaneously facing health challenges, so my journaling turned again to this concept of YOLO.

As I sat watching a bumblebee flit from flower to flower, and a chipmunk dart around a fallen log, I found that YOLO, again, felt really different. 

If you only live once, I thought, you’d better not miss it. 

I considered all the time I’d spent in my youth, dreaming of the future I would create. Back then, I jumped on multiple planes every week chasing the big exit that would change everything. I traveled abroad with a checklist, sprinting from sight to sight to make sure we saw everything. I missed so many beautiful nights searching for shooting stars.

That day, as I allowed myself to really, truly, consider the idea of my life ending, what I found was a strong desire to slow down. 

There’s this exercise I sometimes use with groups of CEOs during which I ask them to contemplate their own mortality as a way of gaining clarity on what’s truly important to them. I ask them to journal on what they would do if they learned they would die in 10 years. We share, and then I ask them to journal on what they would do if they learned they had only a year. Then only a month. And finally, only a day. 

During my day at the cabin, when I reflected on that exercise, I realized that I found myself wanting to move more slowly the less time that’s available to me. 

Sitting on a bench outside Thoreau, I found that I couldn’t even put myself in the frame of mind during which my previous reaction to YOLO made sense. In the face of your own end, missing the time you have because you’re in a rush to fit more activities into it seemed like just about the most asinine thing I could do. We each have been gifted in our lives perhaps 0.000000000001% of all the potential experiences available to human beings. What an odd decision to rush through life at a breakneck speed, missing the bumblebees and flowers and the simple, benign wonder of each experience, simply to shift that number to 0.00000000001%.

I found myself laughing at the thought of it. 

The Augustus quote finishes with a third verse: 

But the man of age, if he plays his assigned role properly, must see life as a comedy. For his triumphs and his failures merge, and one is no more the occasion for pride or shame than the other; and he is neither the hero who proves himself against those forces, nor the protagonist who is destroyed by them.

I seem to have reached the phase of life, perhaps the first of many, in which people begin to lose things. A good friend is grappling with a terminal diagnosis. A mentor, hugely instrumental in the development of my early career, has entered hospice. A close family member is staring down the barrel of cognitive decline. 

YOLO is very real to me, now. But the closer and more personal it gets, the more different it looks. Endings, long a theoretical concept that happened only to other people, are touching me in increasingly intimate ways. And unlike previous chapters, I’m allowing them to touch me. I’m not running away from inevitability, but rather leaning into it, seeking to learn its lessons. 

To me, it feels like the only logical response to the fact that you will only live once, is to slow down. 

Drastically. 

To stop searching intently for the big buck walking through the woods.

And simply watch the bumblebees. 

–

Every night, my oldest son leaves his bedside light on after he falls asleep. This after I’ve told him dozens of times to turn it off before he goes to sleep. It’s a pain in the ass to have to remember for him, and makes it take 45 seconds longer for me to get to bed at night. 

But each time I walk into his room to switch it off, it’s also an opportunity to feel the visceral, overwhelming love I have for that little fucker. 

And these days I try to remember to soak it in. 

Because what YOLO really means is that, at some point, he’ll remember to turn off his own light. 

I don’t know exactly what a prayer is.

I do know how to pay attention, how to fall down

into the grass, how to kneel down in the grass,

how to be idle and blessed, how to stroll through the fields,

which is what I have been doing all day.

Tell me, what else should I have done?

Doesn’t everything die at last, and too soon?

Tell me, what is it you plan to do

with your one wild and precious life?

~ Mary Oliver

---

If you liked reading this, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏

---

---

Want to dive deeper?

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites:

• The secret to leadership (why authentic leadership is simply more effective)

• How to fix your cofounder relationship in 3 difficult steps

• The five practices to transform from founder to CEO

• Finding purpose after exiting your company

• How to pitch a big vision to investors without setting yourself up to let people down

Executive Coaching for Entrepreneurs

I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency built by entrepreneurs, for entrepreneurs.

Through a unique combination of deep executive coaching and strategic execution support, Inside-Out has supported entrepreneurs leading some of the fastest growing companies in the world to develop into world-class leaders, and build high-performance, low-drama companies.

We coach leaders how we want to be coached:

• Focused on the person, not the role.

• Focused on results, without the fluff.

To learn more about working with I-O,  click here.